Phosphorus oxychloride → 2-Bromo-4-chloropyridin-3-ol

HRID 1846237Notes

Reaction equation

HRID 1846237 reaction equation
[Br:1][C:2]1[C:7]([O:8]C)=[C:6]([Cl:10])[CH:5]=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)=O.COC1C(=O)C=CNC=1Br>>[Br:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 497615912-Bromo-3-methoxypyridin-4-olHCID 866967432-Bromo-4-chloro-3-methoxypyridine

Product 1

HCID 722139992-Bromo-4-chloropyridin-3-ol

Conditions

Temperature
20 °C

Procedure

2-bromo-4-chloro-3-methoxypyridine. Phosphorus oxychloride (10 eq.) and 3-methoxy-2-bromo-4(1H)-pyridone (1 eq.) are stirred at 90° C. for 18 h, concentrated in vacuo, and cooled to 20° C. The residue is treated with ice water and adjusted to pH 12 with 40% NaOH, and the product is extracted into DCM. The residue obtained on evaporation of the combined extracts is distilled at reduced pressure to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is treated with ice water
  3. extractionthe product is extracted into DCM
  4. customThe residue obtained on evaporation of the combined extracts
  5. distillationis distilled at reduced pressure

Sources & evidence

ORD record
ord-6f3984306a1c4420b795d126c90c0480
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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